Dynamic kinetic resolutions of alpha-stereogenic-beta-formyl amides in asymmetric 2-aza-Cope rearrangements are described. Chiral phosphoric acids catalyze this rare example of a non-hydrogenative DKR of a beta-oxo acid derivative. The [3,3]-rearrangement occurs with high diastereo- and enantiocontrol, forming beta-imino amides that can be deprotected to the primary beta-amino amide or reduced to the corresponding diamine.